3-(carbamoylamino)-2-(3-methylbenzenesulfonamido)propanoic acid

• ChemBase ID: 179393
• Molecular Formular: C11H15N3O5S
• Molecular Mass: 301.3189
• Monoisotopic Mass: 301.0732416
• SMILES: NC(=O)NCC(NS(=O)(=O)c1cc(ccc1)C)C(=O)O
• Canonical SMILES: NC(=O)NCC(C(=O)O)NS(=O)(=O)c1cccc(c1)C
• InChI: InChI=1S/C11H15N3O5S/c1-7-3-2-4-8(5-7)20(18,19)14-9(10(15)16)6-13-11(12)17/h2-5,9,14H,6H2,1H3,(H,15,16)(H3,12,13,17)
• InChIKey: VKVJFDAJKFKIDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(carbamoylamino)-2-(3-methylbenzenesulfonamido)propanoic acid
• IUPAC Traditional name: 3-(carbamoylamino)-2-(3-methylbenzenesulfonamido)propanoic acid
• Synonyms: 3-[(Aminocarbonyl)amino]-N-[(4-methylphenyl)sulfonyl]-L-alanine; 2-(p-Toluenesulfonamido)-3-ureidopropionic Acid; β-Ureido-L-α-tosylaminopropionic Acid

Database IDs

• PubChem SID: 164235303
• PubChem CID: 71752887

CALCULATED PROPERTIES

• Acid pKa: 3.137968
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.6407185
• LogD (pH = 7.4): -3.7616901
• Log P: -0.3053691
• Molar Refractivity: 70.054 cm^3
• Polarizability: 27.779306 Å^3
• Polar Surface Area: 138.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 174-179°C dec.

DETAILS

Toronto Research Chemicals - U825005

Used in the synthesis of some isomers of Albizziine (D-Albizziine, D-Isoalbizziine, and DL-Isoalbizziine). Also used in the syntheses of MTX analogs derived from 2,ω-diaminoalkanoic acids, as antifolates.

REFERENCES

• Kjaer, A., et al.: Acta Chem. Scandinavica, 14, 961 (1960)
• Piper, J.R., et al.: J. Med. Chem., 28, 1016 (1960)